Another story by Mr. S for the Saturday afternoon ;)
Once again nice writing from dominant point of view ;)
Hope you sissy gurls have a nice weekend!
The Happy Ending
By Mr. S
I’m a fairly firm dominant but even I understand that a well behaved sissy can deserve a full orgasm from time to time. Every other week or so I like to hang a gurl upside down and vibe her ass pussy until I milk her and she oozes onto her own face. That’s fun for me to watch but it’s not the true orgasm that a good sissy can earn from time to time. I’m not saying I make it easy or necessarily fun. Here’s one example of a complete sissy orgasm.
It’s a little after 5 pm on a Saturday and I’m relaxing on the back porch with a Manhattan (my favorite cocktail) and a book about Russian artists. You are just finishing the dishes as we eat dinner early on the weekends. I like to eat around 4 so I’m digested and relaxed when we go out. You come outside, curtsey, and stand in front of me awaiting your next orders.
“Well, sissy,” I say as I fold the book closed, “you’ve been doing some good work lately and I have noticed your improved attention to detail. Why don’t you go take a bath for an hour and then I’ll take you out for a special treat.”
It doesn’t take more than that to send you scampering off to the bathroom. It’s already been a long day of housework and you are eager to take a luxurious bath and equally ready to get out of the tight fitting and restrictive maid’s uniform I demand you wear. In a matter of minutes, the uniform is properly folded and you are in a warm bubble bath soaking away. After bathing, shaving, and relaxing for the full hour you get out, dry off, fix your makeup, style your hair, and leave the bathroom for the bedroom. Before you get to your clothes you see a very sizeable bright red butt plug and lube. Working slowly, you ease the plug into your ass. I have laid out a very simple outfit: black lace crotchless panties (is there anything better than a sissy in chastity and crotchless panties?), a black lace bra, a slinky knee length black dress, and a pair of 4 inch heels. You’re dressed quick and out to see me in the foyer.
“Ready for your treat? Hop in the car and we’ll get going.” You get into the car with me and we take a short drive to a strip mall where I escort you into a nondescript storefront. We enter and I quietly speak to an elderly Asian woman behind the counter. You realize we are at a massage parlor. The woman behind the counter escorts us to a back room with a desk full of supplies, two chairs, and a large massage table. Before she leaves, she instructs you to strip down to your underwear. As she closes the door you look nervously at me, knowing your crotchless panties won’t hide anything.
“You’d better do as you’re told tonight,” I comment, “or you might not get the happy ending you want.” Following my direction you nervously strip, blushing slightly. After removing all your clothes save your panties you nervously stand in the center of the room waiting to find your fate.
The door opens and a stunning young Asian woman glides in wearing the shortest skirt and highest heels you have ever seen. Your first instinct is to be jealous of such a sexy woman. She walks to where I’m seated and speaks to me quietly before returning to you.
“Good evening. I will be taking care of you. You may address me as Miss Kim.” She looks you over and adds, “Why don’t you just take off those ridiculous panties? They’re not hiding anything.” With that she chuckles and your light blush turns deep red. As you shakily take down your panties you immediately feel shame. This young lady, working at a massage parlor, is laughing at you. You are being teased by a glorified prostitute. “Lie down on the table and I’ll start on your back.
You comply and get on the table. She starts high on your neck and works down. She’s quite good and it feels great. Working down your back she loosens all the muscles and you begin to relax and forget any nervousness or unease. She begins working the back of your legs but abruptly stops.
“What’s this?” She asks, poking your butt plug. “It’s my butt plug,” you sheepishly reply. “Why do you have it? It can’t be comfortable,” she questions further. “My master has me wear it to keep me ready for sex and to improve my behavior.” You barely get this humiliating phrase through your lips. She giggles again and the shame hits you like a locomotive. “OK, we’ll leave it there then. It’s kind of cute, anyway.” Now you are devastated.
She finishes your back and asks you to roll over. You do and again she starts up on your neck and works down. After the arms and chest she again perks up and asks, “What’s this?” as she clicks her fingernail on your chastity tube. This time you go deeper into desperate humiliation because you must look at her giggly, smiling face. “That’s my chastity device. Master makes me wear it so I can only climax with his permission!” you blurt out hoping to move on quickly.
“Does it work?”
“So you can’t get hard at all?”
“Can you pee with it on?”
“Only while sitting.”
More giggles. The shame is unbearable at this point. You close your eyes and try to pretend you are somewhere else. Anywhere. Explaining your sissy lifestyle to this whore is degrading to the point where you want to run away. You glance my way for help but I’m reading my book, disinterested in what’s going on. You snap back to the issue at hand as Miss Kim begins to play with your chastised cock. In bewilderment you stammer through a feigned resistance but it stifles on your lips.
“It looks very uncomfortable to me. Especially since you are expanding inside of it.” She is on to you. All the humiliation and now her teasing hands have gotten your blood flowing and now your clitty is pushing the walls of its cell. “It is uncomfortable but I’m used to it,” you get out. More giggles.
“Excuse me, sir but do you think we could remove this?” comes from Miss Kim to me.
“Sure.” I walk over and pull a pair of handcuffs from my pocket. I pull your hands under the table and lock them there. Standing again, I hand Miss Kim the key to the chastity lock.
“Why the cuffs?” she asks.
“We have a rule,” I reply, “Sissy’s clit and hands are never free at the same time. It helps avoid accidents.” More giggles and waves of humiliation.
Before you really have time to react, you hear the click of Miss Kim opening your chastity lock. She fumbles a bit with the pieces but gets them off, handing them to me. I walk to the desk, put down the pieces, and return to my book. This makes you nervous and excited. Miss Kim toys with your clit and you are fully sprung immediately. She expertly tugs and twists, bringing you to the edge of orgasm and then stops and walks away. You look around, panting nervously. It’s been about two months since your last true orgasm and being denied while this close is unbearable.
Miss Kim returns to the table and gently pokes your erect clit. “You should know your master has paid me to keep you on edge for an hour. He also said I can do whatever I want with you.” If you really want to get an orgasm out of this you should start begging me now.” Your mind races. Had I really given this woman control of you? Who begs a hooker for an orgasm? “I said you should start begging now,” snapped Miss Kim before you have a chance to sort your thoughts.
“Please may I have an orgasm, Miss Kim?”
“We’ll see. Keep begging. I’m going to keep you on edge for a little while.”
The next hour creeps by agonizingly slow. Miss Kim does her job of keeping you constantly on edge but never letting even the slightest hint of an orgasm happen. Not only does the teasing drive you crazy but she keeps encouraging your begging. She insists you call her the “Queen of Release”, she makes you ask to have your butt plug removed and reinserted multiple times, she makes you sing nursery rhymes to humiliate you further. All the while her gentle little hands keep your sissy clit hard and constantly ready to spurt.
“I think I should get a happy ending before you do,” explains Miss Kim. In your lost horny stupor you don’t realize what she’s saying but you watch as she takes off her panties from under her tiny skirt and kicks them to the side of the room. Adeptly she leaps onto the table and straddles your head. You look up and to your shocked surprise see that Miss Kim has a cock! “You’re a trans…” is all you can get out before she stuffs her mighty she-cock into your mouth.
She pumps your face for a while, pushing deep to your throat. You handle it fairly well because she’s nowhere near my size but that doesn’t mean she can’t hump your mouth with attitude. The hardest part is the humiliation of being face fucked by a tranny hooker. This isn’t a relaxing blowjob for a friend of mine by his private pool. She maintains teasing your clit the whole while and you are kept at the breaking point. Eventually she stops and pulls her dick out of your mouth.
“Open your mouth and I’m gonna put my balls in it,” she orders. You comply. “Lick my hot lady balls while I talk.” You tongue her soft sack filling your mouth. “You’ve been a good sissy all night and I think I will reward you with a nice, big cum. Before I do I want you to do exactly what I say. I want to play a little game with you. We’ll call it ‘How far sissy can put her tongue up Miss Kim’s ass?’”
With that she tugs her balls out of your mouth and rocks back, putting her ass on your face. “Get that tongue out or we can’t play!” she yells. Slowly you push your tongue out and into her ass. She moans as it gets deeper and deeper. She responds by pushing more of her weight on you, crushing your head between her butt cheeks. Breathing gets challenging and you begin to struggle and squirm in an attempt to keep your air, your calm, and your tongue position. You’ve come so far tonight, don’t lose it now. Your movement gets the attention of Miss Kim and she giggles again, reminding you that at this very moment you are tonguing a whore’s ass.
Miss Kim doesn’t waste any time once you are in the right position. She quickly jacks off her cock and after a very short time shoots ropes of cum on your chest. You feel her tighten with climax and relax once it is over. As a result you ease yourself expecting a rest. “The game isn’t over,” she barks. “Keep that tongue in my whore ass!” Humiliated, you obey her and feel her wipe her load with her hand and use her cum to jerk your clit. It’s humiliating and degrading but at this point you’ll take anything. Once again Miss Kim is quick and efficient and in seconds you are erupting violently in her hand. After a while in chastity with only little milkings, you cum loads and she pumps it all out with vigor. It feels great and your mind and body are blown.
Miss Kim sits up and you take a deep breath for the first time in a few minutes. She takes the opportunity to stuff her cum soaked hand into your open mouth. She climbs off the table like an acrobat all the while holding her hand in your mouth. “Get all that yummy cum, sissy,” she tells you and you suck her hand clean slowly over the course of a few minutes. While you finish with her you feel me replace the chastity tube and lock and then free your hands. Miss Kim and I help you to sit upright and then she leaves us alone in the room.
“Have fun?” I ask.
“Umm…” you mumble out. “Um yes… I think.”
I smile big knowing you are lost in the experience. Tears have been streaming down your face and your makeup is blurred from a combination of them and a grinding whore’s ass. Your chest glistens with Miss Kim’s drying cum and your still twitching clit hugs its prison walls. I put on your panties and bra and pull your dress over your head. I escort you (more like carry you) out to the car to go home but you are asleep before we leave the parking lot.